Devin’s Ladyboy Dating 2

Admin note: Devin originally wrote this in early April, 2012.

My second week back in Bangkok started a bit slowly, but ended with bang or two. I was actually busy dating with some naturally born Thai women during the first part of the week. I have to admit that my preference tends to lean a bit towards ladyboys at this stage of my life and I am certainly more aroused by them.

I happened to see a girl (I will call her P) online in the afternoon and sent a quick hello to her. P is from the south of Thailand and I usually just send her short messages to stay in touch until she makes her way to Bangkok for work. I was surprised when she replied that she was in Bangkok and would like to meet with me. I eagerly accepted her offer and we decided to meet for dinner near my place.

I had met P about a year earlier after chatting and having some fun online with her. Like so many ladyboys, she works as a makeup artist. Her work in Bangkok usually involves joining with a ladyboy friend of hers and that causes problems for me. I was pretty certain her friend would be with her again this time just as she was the first time we met for dinner. That meeting ended with a simple goodbye after finishing our meal and I was confident that this one would too.

It isn’t that I don’t like her friend or that she is unattractive, it’s just that she is a bit bigger than and not quite as feminine as what I prefer. Plus she looks worse next to P who is really cute and has a great body with nice implants. I just want to get with P so much that her friend ends up being an odd third wheel.

I was waiting at the restaurant when P called to tell me that she and, sure enough, her friend would be a few minutes late. It didn’t surprise me and I had already gotten a table for 3. They arrived and P was looking as sexy as ever. Her friend actually looked better than I remembered, but still not the style of ladyboy I would want to date. We had a nice dinner and talked about their work along with other news from the past year.  I was sad to hear that P would be traveling back home the next day.

We all went for ice cream afterwards and I was delighted when they asked to take a look at my apartment. I wasn’t sure exactly what they had in mind, but I figured I may have to accept P’s friend into any extracurricular activity. It was a sacrifice I decided I would be willing to make as we made our way back to my room.

I sat down on the bed and the 2 ladies sat across from me in chairs. P was pretty quiet as her friend was asking all sorts of questions about this and that. I could tell that some of the talk was supposed to lead to other things, but I just didn’t feel like putting on a show for P’s friend. I was a little worried that things would end up with P’s friend and I getting involved while P looked on from the side. I guess I kept things sufficiently boring and P’s friend eventually decided to lie down in the bed and take a nap.

This was my chance to have some time alone with P and I moved over to sit with her on the couch. I let P know how much I liked her and we started to explore a bit. She was a little resistant to some of my advances and explained to me that she would normally be more aggressive but she had just had a recent hormone injection. I was disappointed to hear that and tried my best to convince her that she was sufficiently horny to have some fun with me. In the end I managed to make my way to third base, but the home run would have to wait for another day. I’m really hoping I get that chance with P again soon and I told her as much when she left with her friend that night.

I suppose it might have been the unfinished business from my meeting with P that led me to call on M the next day. As you may recall, M is the young ladyboy I met with a couple times during my first week back in Bangkok. She was happy to see me again and provided another great massage with an even better ending.

The next evening I set up a meeting with a ladyboy I will call KS. It was a sort of rushed meeting as she informed me that she will be leaving town for the holiday and I didn’t want to wait until after that to see her. I jumped in a taxi and headed her way as she was finishing her work day. Half way across town it started to rain cats and dogs. I didn’t know whether or not to continue, but KS messaged me and said that she would wait for me.

I managed to make it into the KFC where she was seeking shelter from the downpour and we had a long conversation over french fries. KS was in her mid 20’s and had a very cute face with short hair. She was tall and slim with noticeable implants. All around a great looking girl and fun to talk to. She seemed to be attracted to me as well and promised to meet again after the holidays when things were a bit dryer. I’m looking forward to seeing KS again.

The last girl I met this week was another tall, very attractive ladyboy in her mid 20’s. PH was someone I had seen online for awhile and I was never quite sure of her looks. It was obvious that she had long and sexy legs, but the face was never clear to me and so I hesitated to contact her. For whatever reason I decided to give it a try and started messaging her. She was nice in the emails and seemed willing to join me for a little fun so we decided to meet at the BTS station near my place.

I was very happy when I saw PH walking my way. She was actually quite attractive and the legs were as good as advertised. She was definitely a northern girl judging by her creamy white skin. She also had a very feminine voice and could easily pass for a lady. We said our hellos and headed straight back to my apartment.

Something interesting happened when we got to my room that made me even more excited than I already was. PH locked and then chained the door behind. I can’t remember a girl doing that before and it just made me realize how much PH wanted to be alone and undisturbed in that room with me. I made my way over to sit on the bed and PH sat across on the couch. We made small talk for awhile and then she got up to answer a call on her phone.

All I could do was stare at those long, slim, milky white legs as she stood there talking. I was just imagining what I was going to be doing with her within the next few minutes. I offered to give her a massage after she got off the phone. She accepted and I was soon caressing her back and giving her sweet kisses on the neck. She had told me before that she was strictly a bottom girl and was perfectly fine with that. I was very gentle with PH and we had an amazing time. It would be hard to find a girl with more smooth, milky skin than her. I’m really hoping I get to see a lot more of PH.

That was it for my week 2 adventures. The big holiday is approaching and may put a dent in dating this week. I can always recall some of my prior encounters if I don’t have much in the way of new activity to report. Until next time, please feel free to comment below.